ZA200204557B - Carbamate derivatives having muscarinic receptor antagonist activity. - Google Patents
Carbamate derivatives having muscarinic receptor antagonist activity. Download PDFInfo
- Publication number
- ZA200204557B ZA200204557B ZA200204557A ZA200204557A ZA200204557B ZA 200204557 B ZA200204557 B ZA 200204557B ZA 200204557 A ZA200204557 A ZA 200204557A ZA 200204557 A ZA200204557 A ZA 200204557A ZA 200204557 B ZA200204557 B ZA 200204557B
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- South Africa
- Prior art keywords
- substituted
- alkyl
- compound
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- amino
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- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title description 4
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 4
- 230000000694 effects Effects 0.000 title description 3
- 239000003149 muscarinic antagonist Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- -1 aminoacyloxy Chemical group 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 8
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 8
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
- 230000001404 mediated effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 206010047513 Vision blurred Diseases 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 206010039424 Salivary hypersecretion Diseases 0.000 claims description 3
- 208000008630 Sialorrhea Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 3
- 125000004476 heterocycloamino group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 229930194542 Keto Natural products 0.000 claims 3
- 125000000033 alkoxyamino group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004470 heterocyclooxy group Chemical group 0.000 claims 3
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 3
- 125000000468 ketone group Chemical group 0.000 claims 3
- 125000005255 oxyaminoacyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000005296 thioaryloxy group Chemical group 0.000 claims 3
- 125000005404 thioheteroaryloxy group Chemical group 0.000 claims 3
- 125000005323 thioketone group Chemical group 0.000 claims 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
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- 125000005647 linker group Chemical group 0.000 description 12
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- 125000004663 dialkyl amino group Chemical group 0.000 description 5
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- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 3
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- 125000005422 alkyl sulfonamido group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 3
- 125000005368 heteroarylthio group Chemical group 0.000 description 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 description 3
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- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 206010063057 Cystitis noninfective Diseases 0.000 description 1
- XIQVNETUBQGFHX-UHFFFAOYSA-N Ditropan Chemical compound C=1C=CC=CC=1C(O)(C(=O)OCC#CCN(CC)CC)C1CCCCC1 XIQVNETUBQGFHX-UHFFFAOYSA-N 0.000 description 1
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- QNOJCNMJPUYJGK-UHFFFAOYSA-N NC(=O)OOOC(N)=O Chemical group NC(=O)OOOC(N)=O QNOJCNMJPUYJGK-UHFFFAOYSA-N 0.000 description 1
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- 206010039966 Senile dementia Diseases 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
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- CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical compound C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45617099A | 1999-12-07 | 1999-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200204557B true ZA200204557B (en) | 2003-09-08 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200204557A ZA200204557B (en) | 1999-12-07 | 2002-06-06 | Carbamate derivatives having muscarinic receptor antagonist activity. |
| ZA200204553A ZA200204553B (en) | 1999-12-07 | 2002-06-06 | Urea compounds having muscarinic receptor antagonist activity. |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200204553A ZA200204553B (en) | 1999-12-07 | 2002-06-06 | Urea compounds having muscarinic receptor antagonist activity. |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US6635764B2 (ko) |
| EP (2) | EP1235803B1 (ko) |
| JP (1) | JP2003516391A (ko) |
| KR (1) | KR100748150B1 (ko) |
| CN (1) | CN1271054C (ko) |
| AT (2) | ATE439345T1 (ko) |
| AU (1) | AU782232B2 (ko) |
| BR (1) | BR0015963A (ko) |
| CA (1) | CA2392030C (ko) |
| CZ (1) | CZ20021830A3 (ko) |
| DE (2) | DE60042762D1 (ko) |
| EA (1) | EA006437B1 (ko) |
| ES (3) | ES2329785T3 (ko) |
| HK (1) | HK1049483B (ko) |
| HR (1) | HRP20020574B1 (ko) |
| HU (1) | HUP0203677A2 (ko) |
| IL (2) | IL149289A0 (ko) |
| IS (1) | IS2191B (ko) |
| MX (1) | MXPA02005602A (ko) |
| NO (1) | NO323544B1 (ko) |
| NZ (1) | NZ518722A (ko) |
| PL (1) | PL364922A1 (ko) |
| SK (1) | SK7982002A3 (ko) |
| UA (1) | UA73543C2 (ko) |
| WO (1) | WO2001042213A1 (ko) |
| YU (1) | YU42402A (ko) |
| ZA (2) | ZA200204557B (ko) |
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| EA200500173A1 (ru) | 2002-07-08 | 2005-08-25 | Рэнбакси Лабораториз Лимитед | Производные 3,6-дизамещенного азабицикло[3.1.0]гексана в качестве антагонистов мускариновых рецепторов |
| TW200800953A (en) * | 2002-10-30 | 2008-01-01 | Theravance Inc | Intermediates for preparing substituted 4-amino-1-(pyridylmethyl) piperidine |
| CN100364990C (zh) * | 2002-10-30 | 2008-01-30 | 施万制药 | 取代的4-氨基-1-(吡啶甲基)哌啶和相关化合物 |
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| CA2584342C (en) | 2004-10-20 | 2013-04-30 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide hydrolase |
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| EP2528604B1 (en) | 2010-01-29 | 2017-11-22 | The Regents of the University of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
| RU2013118026A (ru) * | 2010-10-20 | 2014-10-27 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Карбонатные производные для лечения кашля |
| JP6021616B2 (ja) * | 2012-12-04 | 2016-11-09 | 株式会社アエタスファルマ | ３−ピペラジニル−１−ピペリジニル−プロパン誘導体及びそれを含有してなる医薬組成物 |
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| US6086881A (en) * | 1998-05-15 | 2000-07-11 | Children's Medical Center Corp. | Spatially aligned conjugated composition having a thioether bond linkage |
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| UA73543C2 (uk) * | 1999-12-07 | 2005-08-15 | Тераванс, Інк. | Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором |
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2000
- 2000-07-12 UA UA2002075566A patent/UA73543C2/uk unknown
- 2000-12-07 NZ NZ518722A patent/NZ518722A/en not_active IP Right Cessation
- 2000-12-07 EP EP00982493A patent/EP1235803B1/en not_active Expired - Lifetime
- 2000-12-07 BR BR0015963-8A patent/BR0015963A/pt not_active Application Discontinuation
- 2000-12-07 ES ES04012859T patent/ES2329785T3/es not_active Expired - Lifetime
- 2000-12-07 AU AU19518/01A patent/AU782232B2/en not_active Expired
- 2000-12-07 KR KR1020027007147A patent/KR100748150B1/ko active IP Right Grant
- 2000-12-07 PL PL00364922A patent/PL364922A1/xx not_active Application Discontinuation
- 2000-12-07 ES ES00983991T patent/ES2243333T3/es not_active Expired - Lifetime
- 2000-12-07 DE DE60042762T patent/DE60042762D1/de not_active Expired - Lifetime
- 2000-12-07 CZ CZ20021830A patent/CZ20021830A3/cs unknown
- 2000-12-07 YU YU42402A patent/YU42402A/sh unknown
- 2000-12-07 WO PCT/US2000/033155 patent/WO2001042213A1/en not_active Application Discontinuation
- 2000-12-07 MX MXPA02005602A patent/MXPA02005602A/es active IP Right Grant
- 2000-12-07 CN CNB008167028A patent/CN1271054C/zh not_active Expired - Lifetime
- 2000-12-07 SK SK798-2002A patent/SK7982002A3/sk unknown
- 2000-12-07 DE DE60012223T patent/DE60012223T2/de not_active Expired - Lifetime
- 2000-12-07 HU HU0203677A patent/HUP0203677A2/hu unknown
- 2000-12-07 IL IL14928900A patent/IL149289A0/xx active IP Right Grant
- 2000-12-07 JP JP2001543514A patent/JP2003516391A/ja active Pending
- 2000-12-07 AT AT04012859T patent/ATE439345T1/de not_active IP Right Cessation
- 2000-12-07 CA CA002392030A patent/CA2392030C/en not_active Expired - Lifetime
- 2000-12-07 EP EP04012859A patent/EP1457488B1/en not_active Expired - Lifetime
- 2000-12-07 ES ES00982493T patent/ES2225275T3/es not_active Expired - Lifetime
- 2000-12-07 EA EA200200646A patent/EA006437B1/ru not_active IP Right Cessation
- 2000-12-07 US US09/732,514 patent/US6635764B2/en not_active Expired - Lifetime
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- 2002-04-26 IS IS6362A patent/IS2191B/is unknown
- 2002-06-06 ZA ZA200204557A patent/ZA200204557B/en unknown
- 2002-06-06 NO NO20022683A patent/NO323544B1/no not_active IP Right Cessation
- 2002-06-06 ZA ZA200204553A patent/ZA200204553B/en unknown
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- 2003-03-03 HK HK03101572.1A patent/HK1049483B/zh not_active IP Right Cessation
- 2003-04-30 US US10/426,364 patent/US20040054187A1/en not_active Abandoned
- 2003-04-30 US US10/426,270 patent/US20040116706A1/en not_active Abandoned
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